87567-66-6Relevant academic research and scientific papers
Radical alkenylation of α-halo carbonyl compounds with alkenylindiums
Takami, Kazuaki,Yorimitsu, Hideki,Oshima, Koichiro
, p. 4555 - 4558 (2004)
(Chemical equation presented) Alkenylation reaction of α-halo carbonyl compounds with alkenylindiums proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties as well as a styryl group could be introduced by this metho
Palladium-catalyzed addition of organoboronic acids to allenes
Oh, Chang Ho,Ahn, Tae Won,Reddy V, Raghava
, p. 2622 - 2623 (2007/10/03)
The palladium-catalyzed addition reaction of alkenyl- or aryl-boronic acids into various allenes is described, which allows C-C bond formation in a highly regioselective manner under very mild conditions.
Effect of Microwave Irradiation on the Direction and Stereochemistry of Rodionov and Michael Reactions
Romanova,Gravis,Kudan,Leshcheva,Zyk
, p. 692 - 697 (2007/10/03)
The reactions of 2-phenylpropanal with ethyl hydrogen malonate and benzylamine (or benzyl-ammonium acetate) and of ethyl 4-phenyl-2-pentenoate with benzylamine take different pathways, depending on the conditions.
Stereoseleetive Syntheses of β,γ-Unsaturated Esters and γ-Lactones: 1-(Benzotriazol-1-yl)-3-(diphenylphosphoryl)-1-ethoxy-1-propene, a Protected =CCH2CO2Et Synthon Equivalent
Katritzky, Alan R.,Feng, Daming,Lang, Hengyuan
, p. 4131 - 4136 (2007/10/03)
l-(Benzotriazol-l-yl)-3-(diphenylphosphoryl)-l-ethoxy-l-propene (3), prepared from N-(α-ethoxyallyl)benzotriazole (1), underwent selective Horner reactions with aldehydes to give substituted dienes. Subsequent hydrolysis of these intermediates readily produced β,γ-unsaturated esters 2a-c in good yields. Similar reactions with ketones followed by hydrolysis of 10 produced, depending on the conditions, either the corresponding γ,γ-disubstituted β,γ-unsaturated esters 11a-d or γ-lactones 9a-c and 13. A double lithiation process provided β,γ,γ-trisubstituted β,γ-unsaturated esters 15, 18, and β,γ,γ-trisubstituted γ-lactone 14.
A Stereospecific Access to Allylic Systems Using Rhodium(II)-Vinyl Carbenoid Insertion into Si-H, O-H, and N-H Bonds
Bulugahapitiya, Priyadarshanie,Landais, Yannick,Parra-Rapado, Liliana,Planchenault, Denis,Weber, Valery
, p. 1630 - 1641 (2007/10/03)
Rhodium-catalyzed decomposition of α-vinyldiazoesters in the presence of silanes, alcohols, ethers, amines, and thiols have been shown to produce the corresponding α-silyl, α-hydroxy, α-alkoxy, α-amino, and α-thioalkoxy esters in generally good yield with a complete retention of the stereochemistry of the double bond of the diazo precursor. An extension of the process in homochiral series has also been devised using either a chiral auxiliary attached to the ester function or achiral α-vinyldiazoesters and Doyle's chiral catalyst Rh2(MEPY)4. In the former approach, pantolactone as chiral auxiliary gave diastereoselectivities of up to 70%, while the second approach produced the desired allylsilane with ee as high as 72%. On the other hand, Rh2(MEPY)4-catalyzed insertion into the O-H bond of water led to poor or no enantioselectivity in good agreement with recent literature reports.
